Water → 5-Acetoxy-4,6-di-tert-butyl-2,2-diethyl-2,3-dihydrobenzofuran

HRID 1452362Notes

Reaction equation

HRID 1452362 reaction equation
[C:1]([O:4][C:5]1[C:10]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:9][C:8]([OH:15])=[C:7]([CH:16]=[C:17]([CH2:20][CH3:21])[CH2:18][CH3:19])[C:6]=1[C:22]([CH3:25])([CH3:24])[CH3:23])(=[O:3])[CH3:2].B(F)(F)F.O>ClCCl>[C:1]([O:4][C:5]1[C:10]([C:11]([CH3:12])([CH3:13])[CH3:14])=[CH:9][C:8]2[O:15][C:17]([CH2:20][CH3:21])([CH2:18][CH3:19])[CH2:16][C:7]=2[C:6]=1[C:22]([CH3:23])([CH3:24])[CH3:25])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 6356Boron trifluorideHCID 111000784-Acetoxy-3,5-di-tert-butyl-2-(2-ethyl-1-butenyl)phenol

Product 1

HCID 110244525-Acetoxy-4,6-di-tert-butyl-2,2-diethyl-2,3-dihydrobenzofuranYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Acetoxy-3,5-di-tert-butyl-2-(2-ethyl-1-butenyl)phenol (0.85 g, 2.5 mmol) was dissolved in dichloromethane (10 ml) and BF3 etherate (0.4 ml) was added dropwise to the solution under a nitrogen atmosphere. After stirring at room temperature for 3 h, water was added to the reaction mixture and extracted with ethyl acetate. The extracted layer was washed with a saturated aqueous solution of sodium hydrogen carbonate, dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by silica gel chromatography (10% ethyl acetate in n-hexane) to afford 5-acetoxy-4,6-di-tert-butyl-2,2-diethyl-2,3-dihydrobenzofuran [0.45 g (yield, 53%)] as a pale yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extracted layer was washed with a saturated aqueous solution of sodium hydrogen carbonate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe concentrate was purified by silica gel chromatography (10% ethyl acetate in n-hexane)

Sources & evidence

ORD record
ord-69f44c73dfe843a685b4baeb02a2dc0c
Source dataset
uspto-grants-1997_02
Patent number
US05606089

Reaction notes

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